1999 Trailblazer 4.3 - Hard Starting Cold

My old 1999 S-10 Trailblazer with a 4.3 in it, (Sold it to a good friend of mine) has been giving him problems starting when cold.  He said he will have to crank it a couple times before it starts.  Usually around after 5 times it starts up.  After the truck is running, it runs perfect.  Thanks in advance for your guys help!

Tell him to try turning the key to the on position, and letting it sit, rather than multiple cranking cycles.  This should let the fuel pump prime, and after some seconds in the on position, it should fire right up.  If that works, he''s probably got a dying fuel pump.  A fuel pressure test is a good 2nd step to double check 

We tried to let it sit, and also tried cycleing the key on and off a few times.  We were told it may be the intake plenum.  I saw in a few other posts as well that the plenum was suggested.  I''ll take a fuel pressure test on it to check that as well.  If the pressures good, should I move toward plenum?  Thanks

if the pressure is good going under the plenum wont help, plenum is if pressure drops quickly then usually you move into the plenum to check for clean areas if so then you have a leak at either the regulator or spider. Definitely check out the pressure first so your not doing work/spending cash you dont need to.

I''m having the same symptoms with my 99.  How recently have you changed ignition components?
 
My next test is to plug in my block heater when it gets cold again and see if that makes a difference.